HCID 15158105, compound → HCID 15158134, compound

HRID 703985Notes

Reaction equation

HRID 703985 reaction equation
[Cl:1][C:2]1[CH:7]([C:8]2[C:9]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:10][N:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=23)[CH:6]=[CH:5][N:4](C(OCC)=O)[N:3]=1>[O-2].[Mn+4].[O-2].C(Cl)(Cl)Cl>[Cl:1][C:2]1[N:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[C:9]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[N:10][N:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=12

Participants

4

Reactant 1

HCID 15158105HCID 15158105, compound

Product 1

HCID 15158134HCID 15158134, compoundYield 76.9%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

A mixture of 3-(3-chloro-1-ethoxycarbonyl-1,4-dihydropyridazin-4-yl)-2-phenylpyrazolo[1,5-a]pyridine (1.26 g), manganese (IV) oxide (12.6 g) and chloroform (12.6 ml) was refluxed for 10 hours. After filtration, organic layer was dried over magnesium sulfate. The solvent was removed and chromatographed on silica gel 12.6 g) with a mixture of hexane and ethyl acetate as an eluent. The fractions containing the objective compound were combined and evaporated in vacuo and recrystallized from a mixture of ethyl acetate and n-hexane to give 3-(3-chloropyridazin-4-yl)-2-phenylpyrazolo[1,5-a]pyridine (0.78 g).

Workup

  1. temperaturewas refluxed for 10 hours
  2. filtrationAfter filtration, organic layer
  3. dry with materialwas dried over magnesium sulfate
  4. customThe solvent was removed
  5. customchromatographed on silica gel 12.6 g)
  6. additionwith a mixture of hexane and ethyl acetate as an eluent
  7. additionThe fractions containing the objective compound
  8. customevaporated in vacuo
  9. customrecrystallized from a mixture of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-b1362cc4fd7c419d953dc1c068905860
Source dataset
uspto-grants-1991_01
Patent number
US04985444

Reaction notes

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